IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Study of the impact of nitrogen additions and isothermal temperature on aroma production in oenological fermentation

Nitrogen and temperature are two important factors that influence wine fermentation and volatile compounds production. Among the different compounds present in the must, nitrogen is an essential nutrient for the management of the fermentation kinetics but it also plays an important role in the synthesis of fermentative aromas. To address the problems related to nitrogen deficiencies, nitrogen additions during alcoholic fermentation have been developed.

Correlations between sensory characteristics and colloidal content in dry white wines

Must clarification is an important step occurring just after grape extraction in the elaboration of white wine, consisting in a solid-liquid separation. Traditionally, low must turbidity, around 50-150 NTU, is generally reached in white winemaking in order to prevent reductive aromas and facilitating alcoholic fermentation. Alternatively, a higher turbidity (300 NTU or above) can be sought for reasons such as a better expression of grapes identity (terroir), or for getting a must matrix that could supposedly lead to wines having greater ageing potential.

Production and technological characteristics of some French clones of the Chardonnay variety in Yugoslavia

L’observation est effectuée entre 1996 et 1998. L’expérience a commencé avec des clones numérotés: 75, 95, 96 et 227 de la variété Chardonnay. Le porte greffe est le Kober 5 BB. La forme de conduite est le cordon. La taille est longue. La densité de plantation est 3,5 x 1 mètre (2857 ceps par 1/ha).

A climatic classification of the world’s wine regions and winegrape variety concentration

In this video recording of the IVES science meeting 2024, German Puga (Wine Economics Research Centre, School of Economics and Public Policy, University of Adelaide, Adelaide, Australia) speaks about a climatic classification of the world’s wine regions and winegrape variety concentration. This presentation is based on an original article accessible for free on OENO One.

Comportement du cépage Mourvèdre dans l’aire d’Appellation d’Origine Contrôlée de Bandol

The Appellation d’Origine Contrôlée of Bandol covers an area of ​​1365 ha, 83% of which are planted with vines, the annual production being around 40,000 hl. Among the wines produced, there are mainly reds which assert themselves over time, but also rosés characterized by their pale colour, generally orange; the whites represent a small part of the production. The main grape variety of this AOC is Mouvèdre, of Spanish origin, which is also found in Provence and Languedoc.